Diastereoselective synthesis of highly substituted polycyclic scaffolds via a one-pot four-step tandem catalytic process

作者：Grafton Mark W; Johnson Stuart A; Farrugia Louis J; Sutherland Andrew^*

来源：Tetrahedron, 2014, 70(40): 7133-7141.

DOI：10.1016/j.tet.2014.06.020

• Carbocycles
• Overman rearrangement
• Ring closing enyne metathesis
• Cross metathesis
• Diels-Alder reaction

A rapid and diastereoselective synthesis of highly substituted aminobicyclo[4.3.0]nonanes and bicyclo [4.4.0]decanes from alkyne derived allylic alcohols has been developed using a one-pot multi-bond forming tandem catalytic process. Overman rearrangement of the allylic trichloroacetimidates was followed by a ring closing enyne metathesis/cross metathesis sequence of reactions, in which both steps were catalysed by Grubbs second generation catalyst. The resulting exo-diene was then subjected to a hydrogen bonding directed Diels-Alder reaction forming an endo-adduct as a single diastereomer. Variation of the cross metathesis partner and dienophile allowed examination of the scope of this one-pot process and the preparation of a diverse series of highly substituted polycyclic scaffolds.

• 出版日期2014-10-7